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At forty, Peter, an asylum lawyer in New York City, is overworked and isolated. He spends his days immersed in the struggles of immigrants only to return to an empty apartment and occasional hook-ups with a man who wants more than Peter can give. But when the asylum case of a young gay man pierces Peter's numbness, the event that he has avoided for twenty years returns to haunt him. Ann, his mother, who runs a women's retreat center she founded after leaving his father, is wounded by the estrangement from Peter but cherishes the world she has built.

Newlywed Rosie has grown disenchanted with NYC. Inspired by Instagram ads, she starts thirsting for a rural life upstate—one full of beauty and authenticity. She just needs to convince her tech-bro husband, Jordan, of her vision for the future. Willing to do anything for Rosie’s happiness, Jordan signs on, and they offer—well above asking price—on a beautiful, historic fixer-upper in the Hudson Valley. But when Jordan suddenly loses his job, the couple is forced to rent out the property’s dilapidated outbuilding. There’s no heat, it’s overrun with mold, and nothing works.

Patrick O’Hara is back. It’s been five years since his summer as his niece Maisie and nephew Grant’s caretaker after their mother’s passing. The kids are back in Connecticut with their dad, and Patrick has relocated to New York to remain close by and relaunch his dormant acting career. After the run of his second successful sit-com comes to a close, Patrick feels on top of the world . . . professionally. But some things have had to take a back seat. Looking down both barrels at fifty, Patrick is single again after breaking things off with Emory.

Max Walker is a golden boy. Attractive, intelligent, and athletic, he's the perfect son. Max's mother, a highly successful criminal lawyer, is determined to maintain the facade of effortless excellence she has constructed through the years. Now that the boys are getting older, now that she won't have as much control, she worries that the facade might soon begin to crumble. Adding to the tension, her husband, Steve, has chosen this moment to stand for election to Parliament. The Walkers are hiding something, you see. Max is special. Max is different. Max is intersex.

It’s 2007, and while 43-year-old Leanne Spencer’s career is building up steam, her love life is a trainwreck. She’s always believed her addiction to bad boys stems from her flawless father dying when she was a child, but it turns out Mom’s a liar, Dad’s not dead, and her childhood was a well-crafted illusion.